CA2713713A1 - Derives de piperidine sulfonamide - Google Patents
Derives de piperidine sulfonamide Download PDFInfo
- Publication number
- CA2713713A1 CA2713713A1 CA2713713A CA2713713A CA2713713A1 CA 2713713 A1 CA2713713 A1 CA 2713713A1 CA 2713713 A CA2713713 A CA 2713713A CA 2713713 A CA2713713 A CA 2713713A CA 2713713 A1 CA2713713 A1 CA 2713713A1
- Authority
- CA
- Canada
- Prior art keywords
- methanone
- pyrrolidinyl
- piperidinyl
- formula
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- FLKRMXAWABTWSH-UHFFFAOYSA-N piperidine-1-sulfonamide Chemical class NS(=O)(=O)N1CCCCC1 FLKRMXAWABTWSH-UHFFFAOYSA-N 0.000 title abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 239000002253 acid Substances 0.000 claims abstract description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 208000035475 disorder Diseases 0.000 claims abstract description 10
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- 208000012902 Nervous system disease Diseases 0.000 claims abstract description 9
- 208000025966 Neurological disease Diseases 0.000 claims abstract description 9
- 201000003631 narcolepsy Diseases 0.000 claims abstract description 9
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims abstract description 6
- 208000006199 Parasomnias Diseases 0.000 claims abstract description 6
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims abstract description 6
- 230000027288 circadian rhythm Effects 0.000 claims abstract description 6
- 206010022437 insomnia Diseases 0.000 claims abstract description 6
- 201000002859 sleep apnea Diseases 0.000 claims abstract description 6
- 238000011282 treatment Methods 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 208000019901 Anxiety disease Diseases 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 7
- 230000000926 neurological effect Effects 0.000 claims description 7
- 208000015238 neurotic disease Diseases 0.000 claims description 7
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- 125000003545 alkoxy group Chemical group 0.000 claims description 6
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- SYBHGIDVYKJNEW-UHFFFAOYSA-N [2-(1,3-benzothiazol-2-yl)pyrrolidin-1-yl]-(1-thiophen-2-ylsulfonylpiperidin-3-yl)methanone Chemical compound C1CCC(C=2SC3=CC=CC=C3N=2)N1C(=O)C(C1)CCCN1S(=O)(=O)C1=CC=CS1 SYBHGIDVYKJNEW-UHFFFAOYSA-N 0.000 claims 1
- OHUMWYYTUXKCCW-UHFFFAOYSA-N [2-(1,3-benzothiazol-2-yl)pyrrolidin-1-yl]-[1-(4-fluorophenyl)sulfonylpiperidin-3-yl]methanone Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1CC(C(=O)N2C(CCC2)C=2SC3=CC=CC=C3N=2)CCC1 OHUMWYYTUXKCCW-UHFFFAOYSA-N 0.000 claims 1
- NRVMSDZOKORTDV-UHFFFAOYSA-N [2-(1,3-benzothiazol-2-yl)pyrrolidin-1-yl]-[1-(4-methoxyphenyl)sulfonylpiperidin-3-yl]methanone Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1CC(C(=O)N2C(CCC2)C=2SC3=CC=CC=C3N=2)CCC1 NRVMSDZOKORTDV-UHFFFAOYSA-N 0.000 claims 1
- QBVAVRLVYMFGHC-UHFFFAOYSA-N [2-(2,3-dihydro-1,4-benzodioxin-6-yl)pyrrolidin-1-yl]-(1-thiophen-2-ylsulfonylpiperidin-3-yl)methanone Chemical compound C1CCC(C=2C=C3OCCOC3=CC=2)N1C(=O)C(C1)CCCN1S(=O)(=O)C1=CC=CS1 QBVAVRLVYMFGHC-UHFFFAOYSA-N 0.000 claims 1
- WYGKNUIELFDLRF-UHFFFAOYSA-N [2-(2,3-dihydro-1,4-benzodioxin-6-yl)pyrrolidin-1-yl]-[1-(4-fluorophenyl)sulfonylpiperidin-3-yl]methanone Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1CC(C(=O)N2C(CCC2)C=2C=C3OCCOC3=CC=2)CCC1 WYGKNUIELFDLRF-UHFFFAOYSA-N 0.000 claims 1
- HWIHNKYJMAOQIE-UHFFFAOYSA-N [2-(2,3-dihydro-1,4-benzodioxin-6-yl)pyrrolidin-1-yl]-[1-(4-methoxyphenyl)sulfonylpiperidin-3-yl]methanone Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1CC(C(=O)N2C(CCC2)C=2C=C3OCCOC3=CC=2)CCC1 HWIHNKYJMAOQIE-UHFFFAOYSA-N 0.000 claims 1
- QEHMZJZYSWOCDT-UHFFFAOYSA-N [2-(3,4-dihydro-2h-1,5-benzodioxepin-7-yl)pyrrolidin-1-yl]-[1-(4-fluorophenyl)sulfonylpiperidin-3-yl]methanone Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1CC(C(=O)N2C(CCC2)C=2C=C3OCCCOC3=CC=2)CCC1 QEHMZJZYSWOCDT-UHFFFAOYSA-N 0.000 claims 1
- JBGONXHJWULGCR-UHFFFAOYSA-N [2-(4-ethoxyphenyl)pyrrolidin-1-yl]-(1-thiophen-2-ylsulfonylpiperidin-3-yl)methanone Chemical compound C1=CC(OCC)=CC=C1C1N(C(=O)C2CN(CCC2)S(=O)(=O)C=2SC=CC=2)CCC1 JBGONXHJWULGCR-UHFFFAOYSA-N 0.000 claims 1
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 17
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 14
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
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- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
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- 210000001672 ovary Anatomy 0.000 description 1
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- 125000003373 pyrazinyl group Chemical group 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
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- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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- A61P25/06—Antimigraine agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/96—Sulfur atom
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Addiction (AREA)
- Psychology (AREA)
- Hematology (AREA)
- Pulmonology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08151328 | 2008-02-12 | ||
| EP08151328.5 | 2008-02-12 | ||
| PCT/EP2009/051135 WO2009100994A1 (fr) | 2008-02-12 | 2009-02-02 | Dérivés de pipéridine sulfonamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2713713A1 true CA2713713A1 (fr) | 2009-08-20 |
| CA2713713C CA2713713C (fr) | 2016-05-24 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2713713A Expired - Fee Related CA2713713C (fr) | 2008-02-12 | 2009-02-02 | Derives de piperidine sulfonamide |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US8202888B2 (fr) |
| EP (1) | EP2252587B1 (fr) |
| JP (1) | JP5346043B2 (fr) |
| KR (1) | KR101229603B1 (fr) |
| CN (1) | CN101918361B (fr) |
| AT (1) | ATE517090T1 (fr) |
| AU (1) | AU2009214244B2 (fr) |
| BR (1) | BRPI0907627A2 (fr) |
| CA (1) | CA2713713C (fr) |
| ES (1) | ES2367341T3 (fr) |
| IL (1) | IL206615A (fr) |
| MX (1) | MX2010007968A (fr) |
| WO (1) | WO2009100994A1 (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103079563B (zh) * | 2010-08-24 | 2015-07-08 | 埃科特莱茵药品有限公司 | 作为食欲素受体拮抗剂的脯氨酸磺酰胺衍生物 |
| US9440982B2 (en) | 2012-02-07 | 2016-09-13 | Eolas Therapeutics, Inc. | Substituted prolines/piperidines as orexin receptor antagonists |
| NZ628491A (en) | 2012-02-07 | 2016-06-24 | Eolas Therapeutics Inc | Substituted prolines / piperidines as orexin receptor antagonists |
| ES2901418T3 (es) | 2014-08-13 | 2022-03-22 | Eolas Therapeutics Inc | Difluoropirrolidinas como moduladores del receptor de orexina |
| PT3414241T (pt) | 2016-02-12 | 2022-07-29 | Astrazeneca Ab | Piperidinas substituídas por halo como moduladores de recetores de oxerina |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0115862D0 (en) * | 2001-06-28 | 2001-08-22 | Smithkline Beecham Plc | Compounds |
| WO2004074531A2 (fr) * | 2003-02-13 | 2004-09-02 | Guardian, Industries Corp. | Articles enduits d'une couche nitruree et procedes de realisation associes |
| US20050288317A1 (en) * | 2004-06-24 | 2005-12-29 | Wenqing Yao | Amido compounds and their use as pharmaceuticals |
| CN101133026B (zh) * | 2005-03-03 | 2011-07-06 | 霍夫曼-拉罗奇有限公司 | 作为治疗Ⅱ型糖尿病用的11β-羟基类固醇脱氢酶抑制剂的1-磺酰基-哌啶-3-羧酸酰胺衍生物 |
| US20090118200A1 (en) * | 2005-05-23 | 2009-05-07 | Bergman Jeffrey M | Proline bis-amide orexin receptor antagonists |
| CA2637449A1 (fr) * | 2006-01-23 | 2007-07-26 | F. Hoffmann-La Roche Ag | Derives de cyclohexylsulfonamide presentant une activite vis-a-vis des recepteurs h3 |
| DE602007012072D1 (de) * | 2006-04-26 | 2011-03-03 | Actelion Pharmaceuticals Ltd | Orantagonisten |
| JP2009543790A (ja) * | 2006-07-14 | 2009-12-10 | メルク エンド カムパニー インコーポレーテッド | ２−置換プロリンビス−アミドオレキシン受容体アンタゴニスト |
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2009
- 2009-02-02 ES ES09711149T patent/ES2367341T3/es active Active
- 2009-02-02 EP EP09711149A patent/EP2252587B1/fr not_active Not-in-force
- 2009-02-02 MX MX2010007968A patent/MX2010007968A/es active IP Right Grant
- 2009-02-02 CN CN200980102624.1A patent/CN101918361B/zh not_active Expired - Fee Related
- 2009-02-02 JP JP2010546286A patent/JP5346043B2/ja not_active Expired - Fee Related
- 2009-02-02 AU AU2009214244A patent/AU2009214244B2/en not_active Ceased
- 2009-02-02 BR BRPI0907627-1A patent/BRPI0907627A2/pt not_active Application Discontinuation
- 2009-02-02 WO PCT/EP2009/051135 patent/WO2009100994A1/fr active Application Filing
- 2009-02-02 KR KR1020107017153A patent/KR101229603B1/ko not_active IP Right Cessation
- 2009-02-02 CA CA2713713A patent/CA2713713C/fr not_active Expired - Fee Related
- 2009-02-02 AT AT09711149T patent/ATE517090T1/de active
- 2009-02-05 US US12/365,911 patent/US8202888B2/en not_active Expired - Fee Related
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2010
- 2010-06-24 IL IL206615A patent/IL206615A/en not_active IP Right Cessation
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2012
- 2012-05-23 US US13/478,163 patent/US20120238602A1/en not_active Abandoned
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2013
- 2013-04-02 US US13/855,470 patent/US8691846B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20120238602A1 (en) | 2012-09-20 |
| IL206615A (en) | 2015-10-29 |
| BRPI0907627A2 (pt) | 2015-07-21 |
| JP5346043B2 (ja) | 2013-11-20 |
| IL206615A0 (en) | 2010-12-30 |
| EP2252587A1 (fr) | 2010-11-24 |
| AU2009214244B2 (en) | 2013-02-07 |
| CA2713713C (fr) | 2016-05-24 |
| JP2011511822A (ja) | 2011-04-14 |
| CN101918361B (zh) | 2014-05-28 |
| ATE517090T1 (de) | 2011-08-15 |
| KR20100111709A (ko) | 2010-10-15 |
| KR101229603B1 (ko) | 2013-02-04 |
| CN101918361A (zh) | 2010-12-15 |
| US8202888B2 (en) | 2012-06-19 |
| US20130217729A1 (en) | 2013-08-22 |
| AU2009214244A1 (en) | 2009-08-20 |
| WO2009100994A1 (fr) | 2009-08-20 |
| EP2252587B1 (fr) | 2011-07-20 |
| US8691846B2 (en) | 2014-04-08 |
| US20090203736A1 (en) | 2009-08-13 |
| MX2010007968A (es) | 2010-08-04 |
| ES2367341T3 (es) | 2011-11-02 |
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| EEER | Examination request |
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| MKLA | Lapsed |
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